ID: ALA1164630

Max Phase: Preclinical

Molecular Formula: C15H12ClNO3

Molecular Weight: 289.72

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(/C=C/c1ccc(O)c(O)c1)Nc1cccc(Cl)c1

Standard InChI:  InChI=1S/C15H12ClNO3/c16-11-2-1-3-12(9-11)17-15(20)7-5-10-4-6-13(18)14(19)8-10/h1-9,18-19H,(H,17,20)/b7-5+

Standard InChI Key:  HQSAGGSYGVYRMT-FNORWQNLSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 289.72

Molecular Weight (Monoisotopic): 289.0506

AlogP: 3.40

#Rotatable Bonds: 3

Polar Surface Area: 69.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.22

CX Basic pKa:

CX LogP: 3.57

CX LogD: 3.56

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.60

Np Likeness Score: -0.57

References

1. Fu J, Cheng K, Zhang ZM, Fang RQ, Zhu HL..  (2010)  Synthesis, structure and structure-activity relationship analysis of caffeic acid amides as potential antimicrobials.,  45  (6): [PMID:20181415] [10.1016/j.ejmech.2010.01.066]

2. Shi ZH, Li NG, Shi QP, Tang H, Tang YP, Li W, Yin L, Yang JP, Duan JA..  (2013)  Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors.,  23  (5): [PMID:23375794] [10.1016/j.bmcl.2013.01.027]

3. Fancelli D, Abate A, Amici R, Bernardi P, Ballarini M, Cappa A, Carenzi G, Colombo A, Contursi C, Di Lisa F, Dondio G, Gagliardi S, Milanesi E, Minucci S, Pain G, Pelicci PG, Saccani A, Storto M, Thaler F, Varasi M, Villa M, Plyte S..  (2014)  Cinnamic anilides as new mitochondrial permeability transition pore inhibitors endowed with ischemia-reperfusion injury protective effect in vivo.,  57  (12): [PMID:24918261] [10.1021/jm500547c]

Source

Source(1):

• Scientific Literature